The present invention provides the compound 1-acetyl-3,3-dimethyl-(2-propenyl)cyclohexane and a straight forward, economical process directed towards synthesizing 1-acetyl-3,3-dimethyl-(2-propenyl)cyclohexane by reaction of an allylic halide with acetyl-3,3-dimethylcyclohexane, and utilization of 1-acetyl-3,3-dimethyl-(2-propenyl)cyclohexane for its organoleptic properties in perfumes, perfurmed articles, foodstuffs and medicinal products.
In the perfumery art there is a considerable need for substituents having woody, earthy, sweet, animal aroma characteristics with pineapple/amber nuances and in addition, tobacco/animal aromas. Specifically described are materials having such an economical profile but which do not discolor with age. Such fragrance materials have a wide utilization in the presence of these perfume compounds. A minimum amount of such materials that give rise to these properties is available from natural sources but the natural materials are subject to wide variations in quality, are expensive, and are limited or often in critically short supply.
There is a continuing search for compositions which can vary, fortify, modify, enhance, augment or otherwise improve the flavor and aroma of foodstuffs and medicinal products. To be satisfactory, such compositions should be stable, non-toxic and blendable with other ingredients to provide its own unique flavor and aroma nuance without detracting from the co-ingredients. Preferably, such compositions should be naturally occurring or present in natural foodstuffs so that its ingestible safety can be readily recognized. These materials should be capable of being synthesized in a simple and economical manner. The need for safe flavors in the fruity flavor area, e.g. pineapple, raspberry and other berry-fruit is well-known particularly in the ice cream and yogurt flavor areas and in the cold beverage area. More specifically, there is a need for the development of non-toxic materials which can replace natural materials not readily available, having fruity, pineapple, galbanum and woody aroma characteristics with rosey, ionone-like, oriental and woody flavor characteristics.
Firmenich's Dutch published application 7,500,838 discloses the preparation of the compound having the structure: ##STR2## and discloses its use in perfumery and in augmenting foodstuff flavors. The perfumery use of this compound and other members of its class as "floral, green, herbaceous and chypre" useful in galbanum resinoids is also disclosed.
The compounds disclosed in Dutch published application 7,500,838 have organoleptic properties which causes them to be different in kind from 1-acetyl-3,3-dimethyl-(2-propenyl)cyclohexane, which has unobvious, unexpected and advantageous characteristics in the field of augmenting or enhancing the organoleptic impressions of foodstuffs, foodstuff flavors, perfumes, perfumed articles and medicinal products.
Insofar as relevant prior art concerning the process for preparing 1-acetyl-3,3-dimethyl-(2-propenyl)cyclohexane, German Pat. No. 1,244,784, issued on July 20, 1967, discloses the reaction: ##STR3## wherein R can be one of alkyl, alkenyl, allyl, propargyl, cyclohexyl or benzyl; X is chloro or bromo and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 can be hydrogen, alkyl, alkenyl or phenyl. The reaction of the German Patent is limited to ketones. Although such ketones could be unsaturated, the nature of the reaction is different in kind from the reaction of the instant invention.